EP0889159A2 - Process for pigment dyeing and printing - Google Patents
Process for pigment dyeing and printing Download PDFInfo
- Publication number
- EP0889159A2 EP0889159A2 EP98810586A EP98810586A EP0889159A2 EP 0889159 A2 EP0889159 A2 EP 0889159A2 EP 98810586 A EP98810586 A EP 98810586A EP 98810586 A EP98810586 A EP 98810586A EP 0889159 A2 EP0889159 A2 EP 0889159A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- formula
- alkyl
- dye
- printing
- pigment
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Links
- 0 CC([C@@](C(N(*)C1=O)O)N=Nc(cccc2)c2[N+]([O-])=O)=C1C#N Chemical compound CC([C@@](C(N(*)C1=O)O)N=Nc(cccc2)c2[N+]([O-])=O)=C1C#N 0.000 description 4
- LGJMYGMNWHYGCB-UHFFFAOYSA-N CN(C(C(N1C)O)O)C1=O Chemical compound CN(C(C(N1C)O)O)C1=O LGJMYGMNWHYGCB-UHFFFAOYSA-N 0.000 description 1
- HLMMQBJMGNRPFQ-UHFFFAOYSA-N COC(C(N1CO)OC)N(CO)C1=O Chemical compound COC(C(N1CO)OC)N(CO)C1=O HLMMQBJMGNRPFQ-UHFFFAOYSA-N 0.000 description 1
- NIUDVQRKIOXJST-UHFFFAOYSA-N COCNc1nc(N(CO)COC)nc(N(CO)COC)n1 Chemical compound COCNc1nc(N(CO)COC)nc(N(CO)COC)n1 NIUDVQRKIOXJST-UHFFFAOYSA-N 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Cc1ccccc1 Chemical compound Cc1ccccc1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- MBHRHUJRKGNOKX-UHFFFAOYSA-N Nc1nc(NCO)nc(N)n1 Chemical compound Nc1nc(NCO)nc(N)n1 MBHRHUJRKGNOKX-UHFFFAOYSA-N 0.000 description 1
- ZEYUSQVGRCPBPG-UHFFFAOYSA-N OCN(C(C(N1CO)O)O)C1=O Chemical compound OCN(C(C(N1CO)O)O)C1=O ZEYUSQVGRCPBPG-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0018—Monoazo dyes prepared by diazotising and coupling from diazotized aminopolycyclic rings
- C09B29/0022—Monoazo dyes prepared by diazotising and coupling from diazotized aminopolycyclic rings from diazotized aminoanthracene
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
- C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
- C09B29/3617—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom
- C09B29/3621—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring
- C09B29/3626—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring from a pyridine ring containing one or more hydroxyl groups (or = O)
- C09B29/363—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring from a pyridine ring containing one or more hydroxyl groups (or = O) from diazotized amino carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
- C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
- C09B29/3647—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms
- C09B29/3652—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles
Definitions
- the present invention relates to a method for dyeing or printing fiber material with specific dyes using the pigment dye or pigment printing process.
- pigment printing or pigment dyeing is one of the long-known methods.
- pigment dyes used in processes are often not fully capable of today in particular with regard to sublimation and dry cleaning fastness requirements to suffice.
- the present invention therefore relates to a process for dyeing or printing fiber material by the pigment dyeing or pigment printing process, which is characterized in that a dye liquor or a printing paste containing at least one dye of the formula D - (X) n wherein D represents a residue of an insoluble organic dye of the phthalocyanine, perinone, indigoid, thioindigoid, dioxazine, diketopyrrolopyrrole, isoindolinone, perylene, quinacridone, metal complex, monoazo, disazo, trisazo or anthraquinone series, X is a hydrophilic, polar radical, and n is 1, 2 or 3, and at least one pigment dye binder and, if appropriate, other auxiliaries, are applied to the fiber material and then fixed.
- D represents a residue of an insoluble organic dye of the phthalocyanine, perinone, indigoid, thioindigoid, dioxazine, diketo
- the fiber material is preferably pigmented using a printing paste, containing at least one dye of formula (1), and at least one pigment dye binder as well as any other aids, printed and then fixed.
- Preferred as D is a residue of an insoluble organic dye of monoazo, disazo, Trisazo or anthraquinone series.
- a water-insoluble organic dye is preferably used as the insoluble organic dye Dye understood.
- X in formula (1) denotes a hydrophilic, polar radical, such as, for example, a carbonamido group, a sulfonamido group, where the amido radical in these groups can be mono- or disubstituted with hydroxy-C 1 -C 6 -alkyl, an unsubstituted or by hydroxy substituted C 4 -C 12 alkyl, the alkyl chain being interrupted one or more times by oxygen, carbonamido and / or sulfonamido, or in particular a C 1 -C 6 alkyl which is substituted by one or more hydroxyl groups.
- a hydrophilic, polar radical such as, for example, a carbonamido group, a sulfonamido group
- the amido radical in these groups can be mono- or disubstituted with hydroxy-C 1 -C 6 -alkyl, an unsubstituted or by hydroxy substituted C 4 -C 12 alkyl
- n in the formula (1) is 1, 2 or 3, where (X) n represents one, two or three identical or different radicals X.
- N 1 is preferred.
- Such dyes of the formula (1) are preferred in the process according to the invention used, which have a molecular weight ⁇ 550.
- Dyes of the formula are particularly preferred in the process according to the invention wherein R 8 are hydrogen, methoxy, halogen, nitro or CF 3 and R 9 are hydrogen, methyl, ethyl or hydroxyethyl, wherein R 10 is hydrogen, methoxy, chlorine or nitro, wherein R 11 is C 1 -C 6 alkyl, and
- the dyes of the are very particularly preferred in the inventive method Formulas (10), (11), (12) and (22).
- R 26 is a radical of the formula or is wherein R 16 , R 17 , R 18 , and R 25 have the meaning given under the formulas (5) and (6),
- X is a hydrophilic, polar radical, and the phenyl or naphthyl radical in the formula (27) optionally is substituted by halogen, cyano or nitro, wherein the dyes of the formula (26) must contain at least one radical X.
- the above-mentioned dyes of the formula (26) are prepared by generally known processes, by using a compound of the formula diazotized and coupled to a coupling component of formula (5a), (6a), (27) or (8a). The resulting dye is isolated, washed and dried.
- the pigment dye binders used for the process according to the invention are e.g. Acrylic polymers, such as. Poly (meth) acrylic acid ester, poly (meth) acrylamide or the copolymers of (meth) acrylic acid esters or (meth) acrylamide with suitable comonomers, such as e.g.
- Particularly suitable comonomers are the esters of the abovementioned acids with C 1 -C 6 alcohols, such as, for example, methyl, ethyl, isopropyl or butyl alcohol.
- Well-suited components are polyadducts of 4 to 40 moles of ethylene oxide with 1 mole of a phenol which has at least one C 4 -C 12 alkyl group, a phenyl group, a tolyl group, an ⁇ -tolylethyl group, a benzyl group, an ⁇ -methylbenzyl group or has an ⁇ , ⁇ -dimethylbenzyl group, such as butylphenol, tributylphenol, octylphenol, nonylphenol, dinonylphenol, o-phenylphenol, benzylphenol, dibenzylphenol, ⁇ -tolylethylphenol, dibenzyl- (nonyl) -phenol, ⁇ -methylbenzylphenol, bis- ( ⁇ -methylbenzyl ) phenol or tris ( ⁇ -methylbenzyl) phenol, these adducts can be used individually or in a mixture.
- a phenol which has at least one C 4 -C 12
- Adducts of 6 to 30 moles of ethylene oxide are of particular interest as component (ca) 1 mol of 4-nonylphenol, 1 mol of dinonylphenol or especially 1 mol of compounds, which are prepared by adding 1 to 3 moles of styrenes to 1 mole of phenols.
- the styrene addition products are preferably produced in a known manner Presence of catalysts such as sulfuric acid, p-toluenesulfonic acid or above all Zinc chloride.
- catalysts such as sulfuric acid, p-toluenesulfonic acid or above all Zinc chloride.
- styrenes are styrene, ⁇ -methylstyrene or vinyl toluene (4-methylstyrene).
- the phenols are phenol, cresols or xylenols.
- Ethylene oxide adducts of the formula are very particularly preferred wherein m 3 is 1 to 3 and n 3 is 8 to 30.
- Preferred components (cc) are ethylene oxide adducts with polypropylene oxide (so-called EO-PO block polymers) and propylene oxide adducts with polyethylene oxide (so-called reverse EO-PO block polymers).
- Ethylene oxide-propylene oxide block polymers with molecular weights are particularly preferred the polypropylene oxide base from 1700 to 4000 and an ethylene oxide content in the whole molecule from 30-80%, especially 60-80%.
- the dyes of the formula (1) are applied to the fiber material from a dyeing liquor, this is done, for example, in such a way that the fiber material is mixed with a dyeing liquor which contains at least one dye of the formula (1) and at least one pigment dye binder and, if appropriate, other auxiliaries , treated, the dyed fiber material dries and then fixed by heat treatment.
- the fiber material to be dyed is advantageously treated by a continuous process customary in the textile industry, such as, for example, by a padding process.
- the amounts in which the dyes of the formula (1) are used in the dyeing liquors can vary depending on the desired depth of color, in general quantities of 0.01 to 15 percent by weight, in particular 0.1 to 10 percent by weight of the dyes Formula (1) based on the weight of the material to be dyed has proven to be advantageous.
- the dyeing liquors can, in addition to the dyes of the formula (1) and the pigment dye binders contain other generally customary additives, for example crosslinking resins, such as e.g.
- water-soluble melamine, formaldehyde-melamine and formaldehyde-urea resins or pre-condensates such as trimethylol melamine, hexamethylol melamine or dimethylol urea or water-soluble formaldehyde (pre) condensation products with formamide, thiourea, Guanidine, cyanamide, dicyandiamide and / or water-soluble organic sulfonates such as.
- Sodium salt of naphthalene sulfonic acid, or glyoxal urea derivatives, and especially N-methylol derivatives of nitrogen-containing compounds such as possibly etherified melamine / formaldehyde condensation products or N-methylol-urea compounds also acid donors, e.g. aliphatic amine chlorides or magnesium chloride, aqueous solutions of inorganic salts, e.g. of alkali chlorides or alkali sulfates, alkali hydroxides, Urea, thickenings, e.g. Alginate thickening, water-soluble cellulose alkyl ethers as well as leveling, anti-foaming and / or deaerating agents, penetration accelerators, Migration inhibitors, softening agents and wetting agents.
- acid donors e.g. aliphatic amine chlorides or magnesium chloride
- inorganic salts e.g. of alkali chlorides or alkali sulfates, al
- the dyes of the formula (1) are preferred in a printing paste by a pigment printing process applied to the fiber material.
- the amounts in which the dyes of the formula (1) are used in the printing pastes can vary depending on the desired depth of color, in general amounts of 0.01 to 400 g, in particular 0.5 to 300 g, especially 1 up to 200 g of the dyes per kg of printing paste have proven to be advantageous.
- the printing paste can also contain one or more pigment dyes commonly used in pigment printing technology.
- the printing paste usually contains 1 to 300 g, in particular 50 to 200 g, of the pigment dye binder per kg of printing paste.
- thickeners e.g. those based on poly (meth) acrylic acids, Poly (meth) acrylamides and their copolymers or terpolymers.
- the thickener in the printing paste is preferably in an amount of 0 to 100 g, in particular 10 to 60 g, especially 10 to 40 g per kg of printing paste.
- the printing paste may also contain other auxiliaries which are customary in pigment printing, for example expediently crosslinking agents.
- Suitable crosslinkers are, for example, water-soluble melamine, formaldehyde-melamine and formaldehyde-urea resins or precondensates, such as trimethylolmelamine, hexamethylolmelamine or dimethylolurea or water-soluble formaldehyde (prec) condensation products with formamide, thiourea, guanidine, cyanamide, dicyanodiamine sulfonate and / such as sodium salt of naphthalene sulfonic acid, or glyoxal urea derivatives, such as the compound of the formula and especially N-methylol derivatives of nitrogen-containing compounds such as, for example, etherified melamine / formaldehyde condensation products or N-methylol-urea compounds.
- the optionally etherified N-methylol-urea compounds are e.g. optionally etherified reaction products of formaldehyde with urea or urea derivatives, where, for example, cyclic ethylene or propylene-ureas which also have substituents such as hydroxyl groups in the alkylene group may contain urones or optionally substituted triazone resins.
- N-methylol-urea compounds are optionally modified N-methylol-hydroxyethylene urea products, for example the compounds of the formula or methylolation products based on propylene urea or ethylene urea / melamine.
- Preferred crosslinkers are optionally modified N-methylol-hydroxyethylene urea compounds, methylolation products based on propylene urea or ethylene urea / melamine and in particular optionally etherified melamine / formaldehyde condensation products.
- Mixtures of two or more different water-soluble crosslinking agents can also be used, for example a mixture consisting of an unetherified and an only partially etherified melamine / formaldehyde condensation product.
- the printing paste can also contain crosslinking catalysts, acid donors such as butyrolactone or sodium hydrogenphosphate, preservatives, sequestering agents, emulsifiers, water-insoluble solvents, oxidizing agents or deaerating agents.
- acid donors such as butyrolactone or sodium hydrogenphosphate
- preservatives such as butyrolactone or sodium hydrogenphosphate
- sequestering agents such as butyrolactone or sodium hydrogenphosphate
- emulsifiers such as water-insoluble solvents
- oxidizing agents or deaerating agents such as butyrolactone or sodium hydrogenphosphate
- Suitable crosslinking catalysts for the process according to the invention are, for example, all agents which are customarily used as catalysts for crease and shrink-free finishing, as are known from the Textile Aids Catalog 1991, Konradin Verlag R. Kohlhammer, Leinfelden-Echterdingen 1991.
- suitable crosslinking catalysts are inorganic acids, for example phosphoric acid; Lewis acids, for example zinc chloride, zirconium oxychloride, NaBF 4 , AlCl 3 , MgCl 2 ; Ammonium salts, for example ammonium sulfate, ammonium chloride; or hydrohalides, especially hydrochlorides of organic amines, for example CH 3 -CH 2 -CH 2 -NH-CH 3 . HCl.
- the use of ammonium salts or magnesium-containing Lewis acids and in particular ammonium chloride or magnesium chloride is preferred.
- Suitable preservatives are, above all, formaldehyde-releasing agents, such as, for example, paraformaldehyde and trioxane, especially aqueous, approximately 30 to 40 percent by weight formaldehyde solutions, and sequestering agents, for example sodium nitrilotriacetic acid, sodium ethylenediaminetetraacetic acid, especially sodium polymetaphosphate, in particular sodium hexametaphosphate, as emulsifiers especially adducts of an alkylene oxide and a fatty alcohol, especially an adduct of oleyl alcohol and ethylene oxide, as water-insoluble solvents, high-boiling, saturated hydrocarbons, especially paraffins with a boiling range of about 160 to 210 ° C (so-called mineral spirits), as an oxidizing agent, for example an aromatic nitro compound , especially an aromatic mono- or dinitrocarboxylic acid or sulfonic acid, which is optionally present as an alkylene oxide adduct
- printing machines of conventional design, e.g. Gravure, Rotary screen printing, Rouleaux printing and flat film printing machines useful be used. Printing can also be done using ink-jet printing technology.
- the fiber material is advantageously dried, preferably at temperatures up to 150 ° C, in particular 80 to 120 ° C, and then a heat treatment process subjected to complete the print, or the dye to fix.
- the heat treatment can be carried out by a warm dwell process, a thermal insulation process or preferably be carried out by a damping process (HT fixation).
- HT fixation a damping process
- the printed fiber material is subjected to a treatment in a steamer with possibly superheated steam, advantageously at a temperature of 95 to 210 ° C., advantageously 100 to 180 ° C.
- the printed fiber material is preferably treated for 2 to 5 minutes at 150 to 170 ° C. during HT fixation.
- the prints can be finished by the so-called thermal insulation process after or without intermediate drying, for example at a temperature of 100 to 210 ° C.
- the thermal insulation is preferably carried out at a temperature of 120 to 210 ° C., in particular 140 to 180 ° C. Depending on the temperature, the thermal insulation can take 20 seconds to 5 minutes, preferably 30 seconds to 4 minutes.
- the thermal insulation is usually carried out at 190 to 210 ° C. for 1 to 2 minutes.
- the printed fiber material is washed out in the usual way to remove unfixed dye.
- the fiber material is treated with water, for example at from 40 ° C. to boiling temperature, to which a soap or a synthetic detergent can optionally be added.
- the printing method according to the invention is carried out e.g. in the way that a printing paste containing at least one dye of the formula (1) and at least contains a pigment dye binder and optionally other auxiliaries on the fiber material applies, the printed fiber material dries and then through a Heat treatment fixed.
- the dye liquor or printing paste used according to the invention can be applied to various types of fiber materials, such as wool, silk, cellulose, polyvinyl, polyacrylonitrile, polyamide, aramid, polypropylene, polyester or polyurethane.
- Fiber materials such as wool, silk, cellulose, polyvinyl, polyacrylonitrile, polyamide, aramid, polypropylene, polyester or polyurethane.
- Polyester-containing and cellulose-containing fiber materials are preferred.
- Suitable polyester-containing fiber materials are materials which consist entirely or partially of polyester.
- Celluloseesterfasern such as cellulose-2 1 / acetate 2 and cellulose triacetate fibers, and especially linear polyester fibers, optionally also acid-modified which, for example, by condensing terephthalic acid with ethylene glycol or of isophthalic acid or terephthalic acid with 1,4-bis ( hydroxymethyl) -cyclohexane are obtained, as well as fibers from copolymers of terephthalic and isophthalic acid with ethylene glycol.
- polyester-containing mixed fiber materials ie mixtures of polyester and other fibers.
- Suitable cellulose-containing fiber materials are those materials which are entirely or partly consist of cellulose. Examples are natural fiber materials such as cotton, Linen or hemp, regenerated fiber materials such as Viscose, polynosic or copper artificial silk. Also suitable are cellulose-containing mixed fiber materials, i.e. Mixtures made of cellulose and other fibers, especially cotton / polyester fiber materials.
- Mainly fabrics, knitted fabrics or webs of these fibers are used.
- the dyeings or prints obtainable by the process according to the invention have good general fastnesses; e.g. they have good wet fastness properties, such as washing, water, Fastness to seawater, dyeing and sweating, good chlorine fastness, rubbing fastness, ironing fastness and pleating fastness and are characterized by a high color strength and a brilliant Hue off.
- they are distinguished by the process according to the invention available dyeings or prints due to very good fastness to light, sublimation and dry cleaning out.
- Example 6 The procedure is as given in Example 6, but instead of 30.6 g, a 21.5% strength is used aqueous, microdispersed formulation of the dye of formula (10) the same The amount of the dye of the formula (11a), the formula (12) or the formula (22a) is obtained also prints with good fastness to light, sublimation and dry cleaning.
- Example 6 The procedure is as described in Example 6, but is used instead of a cotton fabric a polyester fabric, you also get a golden yellow print with good light, sublimation and fastness to dry cleaning.
- Example 6 The procedure is as described in Example 6, but is used instead of a cotton fabric a polyester / cotton 67/33 blend, you also get a golden yellow print with good fastness to light, sublimation and dry cleaning.
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Abstract
Description
Die vorliegende Erfindung betrifft ein Verfahren zum Färben oder Bedrucken von Fasermaterial mit spezifischen Farbstoffen nach dem Pigmenffärbe- oder Pigmentdruck-verfahren.The present invention relates to a method for dyeing or printing fiber material with specific dyes using the pigment dye or pigment printing process.
Das Färben oder Bedrucken von Fasermaterialien nach den sogenannten Pigmentdruck- oder Pigmentfärbeverfahren gehört zu den seit langem bekannten Verfahren. Die in diesen Verfahren eingesetzten Pigmentfarbstoffe vermögen aber oft nicht in vollem Umfang den heute insbesondere hinsichtlich Sublimier- und Trockenreinigungsechtheiten gestellten Anforderungen zu genügen.The dyeing or printing of fiber materials according to the so-called pigment printing or pigment dyeing is one of the long-known methods. The one in these However, pigment dyes used in processes are often not fully capable of today in particular with regard to sublimation and dry cleaning fastness requirements to suffice.
Es wurde nun gefunden, dass man mit dem nachfolgend beschriebenen, erfinderischen Verfahren überraschenderweise eine signifikante Verbesserung der Sublimier- und Trockenreinigungsechtheit von Pigmentdrucken und Pigmenffärbungen erreicht, und somit einen Beitrag zu der erforderlichen Verbesserung dieser Druck- oder Färbeverfahren leisten kann.It has now been found that using the inventive method described below Surprisingly, a significant improvement in the fastness to sublimation and dry cleaning achieved by pigment printing and pigment coloring, and thus a contribution can make the necessary improvement to these printing or dyeing processes.
Gegenstand der vorliegenden Erfindung ist daher ein Verfahren zum Färben oder Bedrucken
von Fasermaterial nach dem Pigmentfärbe- oder Pigmentdruckverfahren, welches dadurch
gekennzeichnet ist, dass man eine Färbeflotte oder eine Druckpaste, enthaltend mindestens
einen Farbstoff der Formel
D einen Rest eines unlöslichen organischen Farbstoffes der Phthalocyanin-, Perinon-, Indigoid-,
Thioindigoid-, Dioxazin-, Diketopyrrolopyrrol-, lsoindolinon-, Perylen-, Chinacridon-,
Metallkomplex-, Monoazo-, Disazo-, Trisazo- oder Anthrachinonreihe bedeutet, X ein hydrophiler,
polarer Rest, und n 1, 2 oder 3 ist, und mindestens einen Pigmentfarbstoffbinder sowie
gegebenenfalls weitere Hilfsmittel, auf das Fasermaterial aufbringt und anschliessend
fixiert.The present invention therefore relates to a process for dyeing or printing fiber material by the pigment dyeing or pigment printing process, which is characterized in that a dye liquor or a printing paste containing at least one dye of the formula
D represents a residue of an insoluble organic dye of the phthalocyanine, perinone, indigoid, thioindigoid, dioxazine, diketopyrrolopyrrole, isoindolinone, perylene, quinacridone, metal complex, monoazo, disazo, trisazo or anthraquinone series, X is a hydrophilic, polar radical, and n is 1, 2 or 3, and at least one pigment dye binder and, if appropriate, other auxiliaries, are applied to the fiber material and then fixed.
Bevorzugt wird das Fasermaterial nach dem Pigmentdruckverfahren mit einer Druckpaste, enthaltend mindestens einen Farbstoff der Formel (1), und mindestens einen Pigmentfarbstoffbinder sowie gegebenenfalls weitere Hilfsmittel, bedruckt und anschliessend fixiert. The fiber material is preferably pigmented using a printing paste, containing at least one dye of formula (1), and at least one pigment dye binder as well as any other aids, printed and then fixed.
Bevorzugt als D ist ein Rest eines unlöslichen organischen Farbstoffes der Monoazo-, Disazo-, Trisazo- oder Anthrachinonreihe.Preferred as D is a residue of an insoluble organic dye of monoazo, disazo, Trisazo or anthraquinone series.
Als unlöslicher organischer Farbstoff wird vorzugsweise ein wasserunlöslicher organischer Farbstoff verstanden.A water-insoluble organic dye is preferably used as the insoluble organic dye Dye understood.
Bevorzugt in dem erfindungsgemässen Verfahren sind Farbstoffe der Formeln
worin
C1-C4-Alkyl oder C1-C4-Alkoxy, R6 Wasserstoff oder Halogen, und R7 Wasserstoff,
C1-C4-Alkyl oder C1-C4-Alkoxy sind, wobei der Farbstoff der Formel (2) mindestens einen
Rest X enthalten muss,
worin
X in der Formel (1) bedeutet einen hydrophilen, polaren Rest, wie z.B. eine Carbonamidogruppe, eine Sulfonamidogruppe, wobei der Amidorest in diesen Gruppen mit Hydroxy-C1-C6-alkyl mono- oder disubstituiert sein kann, ein unsubstituiertes oder durch Hydroxy substituiertes C4-C12-Alkyl, wobei die Alkylkette ein- oder mehrfach durch Sauerstoff, Carbonamido und/oder Sulfonamido unterbrochen ist, oder insbesondere ein C1-C6-Alkyl welches mit einem oder mehreren Hydroxygruppen substituiert ist.X in formula (1) denotes a hydrophilic, polar radical, such as, for example, a carbonamido group, a sulfonamido group, where the amido radical in these groups can be mono- or disubstituted with hydroxy-C 1 -C 6 -alkyl, an unsubstituted or by hydroxy substituted C 4 -C 12 alkyl, the alkyl chain being interrupted one or more times by oxygen, carbonamido and / or sulfonamido, or in particular a C 1 -C 6 alkyl which is substituted by one or more hydroxyl groups.
n in der Formel (1) ist 1, 2 oder 3, wobei (X)n für eine, zwei oder drei gleiche oder verschiedene Reste X steht. n in the formula (1) is 1, 2 or 3, where (X) n represents one, two or three identical or different radicals X.
Bevorzugt ist n = 1.N = 1 is preferred.
Bevorzugt werden in dem erfindungsgemässen Verfahren solche Farbstoffe der Formel (1) verwendet, welche ein Molekulargewicht < als 550 haben.Such dyes of the formula (1) are preferred in the process according to the invention used, which have a molecular weight <550.
In dem erfindungsgemässen Verfahren sind besonders bevorzugt Farbstoffe der Formel
worin
R8 Wasserstoff, Methoxy, Halogen, Nitro oder CF3 und R9 Wasserstoff, Methyl, Ethyl oder
Hydroxyethyl sind,
worin
R10 Wasserstoff, Methoxy, Chlor oder Nitro ist,
worin
R11 C1-C6-Alkyl ist,
und
Dyes of the formula are particularly preferred in the process according to the invention wherein
R 8 are hydrogen, methoxy, halogen, nitro or CF 3 and R 9 are hydrogen, methyl, ethyl or hydroxyethyl, wherein
R 10 is hydrogen, methoxy, chlorine or nitro, wherein
R 11 is C 1 -C 6 alkyl, and
Ganz besonders bevorzugt sind in dem erfindungsgemässen Verfahren die Farbstoffe der Formeln (10), (11), (12) und (22).The dyes of the are very particularly preferred in the inventive method Formulas (10), (11), (12) and (22).
Einen weiteren Gegenstand der vorliegenden Erfindung stellen die Farbstoffe der Formel
worin
R26 ein Rest der Formel
oder
ist,
worin R16, R17, R18, und R25 die unter den Formeln (5) und (6) angegebene Bedeutung haben,
X einen hydrophilen, polaren Rest bedeutet, und der Phenyl- bzw. Naphthylrest in der
Formel (27) gegebenenfalls durch Halogen, Cyano oder Nitro substituiert ist, dar, wobei die
Farbstoffe der Formel (26) mindestens einen Rest X enthalten müssen.Another object of the present invention are the dyes of the formula wherein
R 26 is a radical of the formula or is
wherein R 16 , R 17 , R 18 , and R 25 have the meaning given under the formulas (5) and (6), X is a hydrophilic, polar radical, and the phenyl or naphthyl radical in the formula (27) optionally is substituted by halogen, cyano or nitro, wherein the dyes of the formula (26) must contain at least one radical X.
Die Herstellung der obgenannten Farbstoffe der Formel (26) geschieht nach allgemein bekannten Verfahren, indem man eine Verbindung der Formel diazotiert und an eine Kupplungskomponente der Formel (5a), (6a), (27) oder (8a) kuppelt. Das entstandene Farbstoff wird isoliert, gewaschen und getrocknet.The above-mentioned dyes of the formula (26) are prepared by generally known processes, by using a compound of the formula diazotized and coupled to a coupling component of formula (5a), (6a), (27) or (8a). The resulting dye is isolated, washed and dried.
Auf analoge Weise können auch die übrigen oben aufgeführten erfindungsgemäss verwendeten Monoazofarbstoffe hergestellt werden.The other above-mentioned can also be used according to the invention in a similar manner Monoazo dyes are made.
Als Pigmentfarbstoffbinder kommen für das erfindungsgemässe Verfahren z.B. Acrylpolymerisate, wie z.B. Poly(meth)acrylsäureester, Poly(meth)acrylamid oder die Mischpolymerisate von (Meth)acrylsäureestern oder (Meth)acrylamid mit geeigneten Comonomeren, wie z.B. Malein-, Fumar-, Itacon-, Mesacon-, Citracon-, Vinylessig-, Vinyloxyessig-, Vinylpropion-, Croton-, Aconit-, Allylessig-, Allyloxyessig-, Allylmalon-, 2-Acrylamido-2-methylpropansulfon-, Glutacon- oder Allylbernsteinsäure oder mit Estern dieser Säuren, N-Vinylpyrrolidon, N-Vinylformamid, N-Vinylacetamid, (Meth)acrolein, N-Vinyl-N-methylacetamid, Vinylcaprolactam, Styrolderivate oder Vinylphosphonsäure; Polyamidderivate; Kunstharzdispersionen; Mischpolymerisate auf Vinylbasis; Diamid-Aldehyd-Vorkondensate; Mischpolymerisate enthaltend N-Vinyllactam oder Polymerisate auf Butadienbasis. The pigment dye binders used for the process according to the invention are e.g. Acrylic polymers, such as. Poly (meth) acrylic acid ester, poly (meth) acrylamide or the copolymers of (meth) acrylic acid esters or (meth) acrylamide with suitable comonomers, such as e.g. Malein, fumar, itacon, mesacon, citracon, vinyl vinegar, vinyloxy vinegar, vinyl propion, Croton-, Aconit-, Allylessig-, Allyloxyessig-, Allylmalon-, 2-Acrylamido-2-methylpropansulfon-, Glutaconic or allylsuccinic acid or with esters of these acids, N-vinylpyrrolidone, N-vinylformamide, N-vinyl acetamide, (meth) acrolein, N-vinyl-N-methylacetamide, vinyl caprolactam, Styrene derivatives or vinylphosphonic acid; Polyamide derivatives; Synthetic resin dispersions; Copolymers based on vinyl; Diamide-aldehyde precondensates; Containing copolymers N-vinyl lactam or butadiene-based polymers.
Als Comonomere geeignet sind insbesondere die Ester von den obengenannten Säuren mit C1-C6-Alkoholen, wie z.B. Methyl-, Ethyl-, Isopropyl- oder Butylalkohol, in Betracht.Particularly suitable comonomers are the esters of the abovementioned acids with C 1 -C 6 alcohols, such as, for example, methyl, ethyl, isopropyl or butyl alcohol.
Die Farbstoffe der Formel (1) werden zweckmässigerweise in der Färbeflotte oder in der
Druckpaste in dispergierter Form eingesetzt.
Dabei werden die Farbstoffe mit dem Dispersionsmittel vorteilhafterweise so vermahlen,
dass eine Farbstoffteilchengrösse zwischen 0,05- 1,0 µm resultiert.
Zur Herstellung der Farbstoffdispersionen können die üblichen Dispergiermittel, vorzugsweise
nichtionogenen Dispergiermittel, verwendet werden.
Als nichtionogene Dispergiermittel eignen sich insbesondere Verbindungen, welche aus der
Gruppe der
(ca) Alkylenoxidaddukte der Formel
worin
The dyes are advantageously ground with the dispersant in such a way that a dye particle size of between 0.05-1.0 μm results.
The customary dispersants, preferably nonionic dispersants, can be used to prepare the dye dispersions.
Particularly suitable nonionic dispersants are compounds which belong to the group of
(ca) alkylene oxide adducts of the formula wherein
Gut geeignete Komponenten (ca) sind Polyaddukte von 4 bis 40 Mol Ethylenoxid an 1 Mol eines Phenols, das mindestens eine C4-C12-Alkylgruppe, eine Phenylgruppe, eine Tolylgruppe, eine α-Tolylethylgruppe, eine Benzylgruppe, eine α-Methylbenzylgruppe oder eine α,α-Dimethylbenzylgruppe aufweist, wie z.B. Butylphenol, Tributylphenol, Octylphenol, Nonylphenol, Dinonylphenol, o-Phenylphenol, Benzylphenol, Dibenzylphenol, α-Tolylethylphenol, Dibenzyl-(nonyl)-phenol, α-Methylbenzylphenol, Bis-(α-Methylbenzyl)-phenol oder Tris-(α-methylbenzyl)-phenol, wobei diese Addukte einzeln oder in Mischung verwendet werden können.Well-suited components (ca) are polyadducts of 4 to 40 moles of ethylene oxide with 1 mole of a phenol which has at least one C 4 -C 12 alkyl group, a phenyl group, a tolyl group, an α-tolylethyl group, a benzyl group, an α-methylbenzyl group or has an α, α-dimethylbenzyl group, such as butylphenol, tributylphenol, octylphenol, nonylphenol, dinonylphenol, o-phenylphenol, benzylphenol, dibenzylphenol, α-tolylethylphenol, dibenzyl- (nonyl) -phenol, α-methylbenzylphenol, bis- (α-methylbenzyl ) phenol or tris (α-methylbenzyl) phenol, these adducts can be used individually or in a mixture.
Von besonderem Interesse als Komponente (ca) sind Addukte von 6 bis 30 Mol Ethylenoxid an 1 Mol 4-Nonylphenol, an 1 Mol Dinonylphenol oder besonders an 1 Mol von Verbindungen, die durch Anlagerung von 1 bis 3 Mol von Styrolen an 1 Mol Phenole hergestellt werden.Adducts of 6 to 30 moles of ethylene oxide are of particular interest as component (ca) 1 mol of 4-nonylphenol, 1 mol of dinonylphenol or especially 1 mol of compounds, which are prepared by adding 1 to 3 moles of styrenes to 1 mole of phenols.
Die Herstellung der Styrolanlagerungsprodukte erfolgt in bekannter Weise vorzugsweise in Gegenwart von Katalysatoren, wie Schwefelsäure, p-Toluolsulfonsäure oder vor allem Zinkchlorid. Als Styrole kommen zweckmässigerweise Styrol, α-Methylstyrol oder Vinyltoluol (4-Methylstyrol) in Betracht. Beispiele für die Phenole sind Phenol, Kresole oder Xylenole.The styrene addition products are preferably produced in a known manner Presence of catalysts such as sulfuric acid, p-toluenesulfonic acid or above all Zinc chloride. Appropriately styrenes are styrene, α-methylstyrene or vinyl toluene (4-methylstyrene). Examples of the phenols are phenol, cresols or xylenols.
Ganz besonders bevorzugt sind Ethylenoxidaddukte der Formel worin m3 1 bis 3 und n3 8 bis 30 bedeuten.Ethylene oxide adducts of the formula are very particularly preferred wherein m 3 is 1 to 3 and n 3 is 8 to 30.
Ebenfalls bevorzugt sind Ethylenoxidaddukte der Formel worin Y2C4-C12-Alkyl, Phenyl, Tolyl, Tolyl-C1-C3-alkyl oder Phenyl-C1-C3-alkyl, wie z.B. α-Methyl- oder α,α-Dimethylbenzyl bedeutet, und m2 1 bis 3 und n2 4 bis 40 sind. Die nichtionogene Komponente (cb) ist vorteilhafterweise
- ein Alkylenoxidanlagerungsprodukt von 1 bis 100 Mol Alkylenoxid, z.B. Ethylenoxid und/oder Propylenoxid, an 1 Mol eines aliphatischen Monoalkohols mit mindestens 4 Kohlenstoffatomen, eines 3- bis 6-wertigen aliphatischen Alkohols oder eines gegebenenfalls durch Alkyl, Phenyl, α-Tolylethyl, Benzyl, α-Methylbenzyl oder α,α-Dimethylbenzyl substituierten Phenols (cba);
- ein Alkylenoxidanlagerungsprodukt von 1 bis 100, vorzugsweise 2 bis 80 Mol Ethylenoxid wobei einzelne Ethylenoxideinheiten durch substituierte Epoxide, wie Styroloxid und/oder Propylenoxid, ersetzt sein können, an höhere ungesättigte oder gesättigte Monoalkohole (cba), Fettsäuren (cbb), Fettamine (cbc) oder Fettamide (cbd) mit 8 bis 22 Kohlenstoffatomen;
- ein Alkylenoxidanlagerungsprodukt, vorzugsweise ein Ethylenoxid-Propylenoxid-Addukt an Ethylendiamin (cbe);
- ein ethoxyliertes Sorbitanester mit langkettigen Estergruppen, wie z.B. Polyoxiethylen-Sorbitanmonolaurat mit 4 bis 20 Ethylenoxideinheiten oder Polyoxiethylen-Sorbitantrioleat mit 4 bis 20 Ethylenoxideinheiten (cbf).
- an alkylene oxide adduct of 1 to 100 moles of alkylene oxide, for example ethylene oxide and / or propylene oxide, on 1 mole of an aliphatic monoalcohol having at least 4 carbon atoms, a 3- to 6-valent aliphatic alcohol or one optionally substituted by alkyl, phenyl, α-tolylethyl, benzyl, α-methylbenzyl or α, α-dimethylbenzyl substituted phenol (cba);
- an alkylene oxide addition product of 1 to 100, preferably 2 to 80, moles of ethylene oxide, where individual ethylene oxide units can be replaced by substituted epoxides, such as styrene oxide and / or propylene oxide, to higher unsaturated or saturated monoalcohols (cba), fatty acids (cbb), fatty amines (cbc) or fatty amides (cbd) with 8 to 22 carbon atoms;
- an alkylene oxide adduct, preferably an ethylene oxide-propylene oxide adduct with ethylenediamine (cbe);
- an ethoxylated sorbitan ester with long-chain ester groups, such as polyoxyethylene sorbitan monolaurate with 4 to 20 ethylene oxide units or polyoxyethylene sorbitan trioleate with 4 to 20 ethylene oxide units (cbf).
Bevorzugte Komponenten (cc) sind Ethylenoxidaddukte an Polypropylenoxid (sogenannte EO-PO-Blockpolymere) und Propylenoxidaddukte an Polyethylenoxid (sogenannte umgekehrte EO-PO-Blockpolymere).Preferred components (cc) are ethylene oxide adducts with polypropylene oxide (so-called EO-PO block polymers) and propylene oxide adducts with polyethylene oxide (so-called reverse EO-PO block polymers).
Besonders bevorzugt sind Ethylenoxid-Propylenoxid-Blockpolymere mit Molekulargewichten der Polypropylenoxidbasis von 1700 bis 4000 und einem Ethylenoxidgehalt im Gesamtmolekül von 30-80%, insbesondere 60-80%.Ethylene oxide-propylene oxide block polymers with molecular weights are particularly preferred the polypropylene oxide base from 1700 to 4000 and an ethylene oxide content in the whole molecule from 30-80%, especially 60-80%.
Werden die Farbstoffe der Formel (1) aus einer Färbeflotte auf das Fasermaterial appliziert,
so geschieht dies z.B. in der Weise, dass man das Fasermaterial mit einer Färbeflotte, welche
mindestens einen Farbstoff der Formel (1) und mindestens einen Pigmentfarbstoffbinder
sowie gegebenenfalls weitere Hilfsmittel enthält, behandelt, das gefärbte Fasermaterial
trocknet und anschliessend durch eine Hitzebehandlung fixiert.
Vorteilhafterweise wird das zu färbende Fasermaterial nach einem in der Textilindustrie üblichen
kontinuierlichen Verfahren, wie z.B. nach einem Foulardverfahren behandelt. If the dyes of the formula (1) are applied to the fiber material from a dyeing liquor, this is done, for example, in such a way that the fiber material is mixed with a dyeing liquor which contains at least one dye of the formula (1) and at least one pigment dye binder and, if appropriate, other auxiliaries , treated, the dyed fiber material dries and then fixed by heat treatment.
The fiber material to be dyed is advantageously treated by a continuous process customary in the textile industry, such as, for example, by a padding process.
Die Mengen, in denen man die Farbstoffe der Formel (1) in den Färbeflotten verwendet, können je nach der gewünschten Farbtiefe schwanken, im allgemeinen haben sich Mengen von 0,01 bis 15 Gewichtsprozent, insbesondere 0,1 bis 10 Gewichtsprozent der Farbstoffe der Formel (1) bezogen auf das Gewicht des Färbegutes als vorteilhaft erwiesen. Die Färbeflotten können ausser den Farbstoffen der Formel (1) und den Pigmentfarbstoffbindern weitere allgemein üblichen Zusätze enthalten, beispielsweise Vernetzerharze, wie z.B. wasserlössliche Melamin-, Formaldehyd-Melamin- und Formaldehyd-Harnstoffharze oder Vorkondensate, wie Trimethylolmelamin, Hexamethylolmelamin oder Dimethylolharnstoff oder wasserlösliche Formaldehyd-(Vor)kondensationsprodukte mit Formamid, Thioharnstoff, Guanidin, Cyanamid, Dicyandiamid und/oder wasserlöslichen organischen Sulfonaten wie z.B. Natriumsalz der Naphthalinsulfonsäure, oder Glyoxalharnstoffderivate, und vor allem N-Methylolderivate von stickstoffhaltigen Verbindungen wie z.B. gegebenenfalls veretherte Melamin/Formaldehyd-Kondensationsprodukte oder N-Methylol-Harnstoff Verbindungen, ferner Säurespender, wie z.B. aliphatische Aminchloride oder Magnesiumchlorid, wässrige Lösungen anorganischer Salze, z.B. von Alkalichloriden oder Alkalisulfaten, Alkalihydroxide, Harnstoff, Verdickungen, wie z.B. Alginatverdickungen, wasserlösliche Cellulosealkyläther sowie Egalisier-, Antischaum- und/oder Entlüftungsmittel, Penetrationsbeschleuniger, Migrationsinhibitoren, Weichgriffmittel sowie Netzmittel.The amounts in which the dyes of the formula (1) are used in the dyeing liquors can vary depending on the desired depth of color, in general quantities of 0.01 to 15 percent by weight, in particular 0.1 to 10 percent by weight of the dyes Formula (1) based on the weight of the material to be dyed has proven to be advantageous. The dyeing liquors can, in addition to the dyes of the formula (1) and the pigment dye binders contain other generally customary additives, for example crosslinking resins, such as e.g. water-soluble melamine, formaldehyde-melamine and formaldehyde-urea resins or pre-condensates such as trimethylol melamine, hexamethylol melamine or dimethylol urea or water-soluble formaldehyde (pre) condensation products with formamide, thiourea, Guanidine, cyanamide, dicyandiamide and / or water-soluble organic sulfonates such as. Sodium salt of naphthalene sulfonic acid, or glyoxal urea derivatives, and especially N-methylol derivatives of nitrogen-containing compounds such as possibly etherified melamine / formaldehyde condensation products or N-methylol-urea compounds, also acid donors, e.g. aliphatic amine chlorides or magnesium chloride, aqueous solutions of inorganic salts, e.g. of alkali chlorides or alkali sulfates, alkali hydroxides, Urea, thickenings, e.g. Alginate thickening, water-soluble cellulose alkyl ethers as well as leveling, anti-foaming and / or deaerating agents, penetration accelerators, Migration inhibitors, softening agents and wetting agents.
Bevorzugt werden die Farbstoffe der Formel (1) in einer Druckpaste nach einem Pigmentdruckverfahren auf das Fasermaterial appliziert.The dyes of the formula (1) are preferred in a printing paste by a pigment printing process applied to the fiber material.
Die Mengen, in denen man die Farbstoffe der Formel (1) in den Druckpasten verwendet,
können je nach der gewünschten Farbtiefe schwanken, im allgemeinen haben sich Mengen
von 0,01 bis 400 g, insbesondere 0,5 bis 300 g, vor allem 1 bis 200 g der Farbstoffe pro kg
Druckpaste als vorteilhaft erwiesen.
Die Druckpaste kann ausser den Farbstoffen der Formel (1) auch einen oder mehrere in den
Pigmentdrucktechnik üblicherweise verwendeten Pigmentfarbstoffe enthalten.The amounts in which the dyes of the formula (1) are used in the printing pastes can vary depending on the desired depth of color, in general amounts of 0.01 to 400 g, in particular 0.5 to 300 g, especially 1 up to 200 g of the dyes per kg of printing paste have proven to be advantageous.
In addition to the dyes of the formula (1), the printing paste can also contain one or more pigment dyes commonly used in pigment printing technology.
Die Druckpaste enthält dabei üblicherweise 1 bis 300 g, insbesondere 50 bis 200 g des Pigmenffarbstoffbinders pro kg Druckpaste. The printing paste usually contains 1 to 300 g, in particular 50 to 200 g, of the pigment dye binder per kg of printing paste.
Vorteilhafterweise enthält die Druckpaste ausser den Farbstoffen der Formel (1) und den Pigmentfarbstoffbinder auch Verdickungsmittel, z.B. solche auf Basis von Poly(meth)acrylsäuren, Poly(meth)acrylamiden, sowie deren Co-, bzw. Terpolymeren.In addition to the dyes of the formula (1) and the Pigment dye binders also thickeners, e.g. those based on poly (meth) acrylic acids, Poly (meth) acrylamides and their copolymers or terpolymers.
Das Verdickungsmittel ist in der Druckpaste vorzugsweise in einer Menge von 0 bis 100 g, insbesondere 10 bis 60 g, vor allem 10 bis 40 g pro kg Druckpaste enthalten.The thickener in the printing paste is preferably in an amount of 0 to 100 g, in particular 10 to 60 g, especially 10 to 40 g per kg of printing paste.
Die Druckpaste kann ebenfalls weitere bei dem Pigmentdruck übliche Hilfsmittel, z.B. zweckmässigerweise
Vernetzer, enthalten.
Als Vernetzer eignen sich z.B. wasserlössliche Melamin-, Formaldehyd-Melamin- und Formaldehyd-Harnstoffharze
oder Vorkondensate, wie Trimethylolmelamin, Hexamethylolmelamin
oder Dimethylolharnstoff oder wasserlösliche Formaldehyd-(Vor)kondensationsprodukte
mit Formamid, Thioharnstoff, Guanidin, Cyanamid, Dicyandiamid und/oder wasserlöslichen
organischen Sulfonaten wie z.B. Natriumsalz der Naphthalinsulfonsäure, oder Glyoxalharnstoffderivate,
wie z.B. die Verbindung der Formel
und vor allem N-Methylolderivate von stickstoffhaltigen Verbindungen wie z.B. gegebenenfalls
veretherte Melamin/Formaldehyd-Kondensationsprodukte oder N-Methylol-Harnstoff
Verbindungen.The printing paste may also contain other auxiliaries which are customary in pigment printing, for example expediently crosslinking agents.
Suitable crosslinkers are, for example, water-soluble melamine, formaldehyde-melamine and formaldehyde-urea resins or precondensates, such as trimethylolmelamine, hexamethylolmelamine or dimethylolurea or water-soluble formaldehyde (prec) condensation products with formamide, thiourea, guanidine, cyanamide, dicyanodiamine sulfonate and / such as sodium salt of naphthalene sulfonic acid, or glyoxal urea derivatives, such as the compound of the formula and especially N-methylol derivatives of nitrogen-containing compounds such as, for example, etherified melamine / formaldehyde condensation products or N-methylol-urea compounds.
Beispiele für die gegebenenfalls veretherten Melamin/Formaldehyd-Kondensationsprodukte sind die Verbindungen der Formeln Examples of the optionally etherified melamine / formaldehyde condensation products are the compounds of the formulas
Bei den gegebenenfalls veretherten N-Methylol-Harnstoff-Verbindungen handelt es sich z.B. um gegebenenfalls nachträglich veretherte Umsetzungsprodukte von Formaldehyd mit Harnstoff oder Harnstoffderivaten, wobei als Harnstoffderivate beispielsweise cyclische Ethylen- oder Propylen-Harnstoffe, die in der Alkylengruppe auch Substituenten wie Hydroxylgruppen enthalten können, Urone oder gegebenenfalls substituierte Triazonharze in Frage kommen.The optionally etherified N-methylol-urea compounds are e.g. optionally etherified reaction products of formaldehyde with urea or urea derivatives, where, for example, cyclic ethylene or propylene-ureas which also have substituents such as hydroxyl groups in the alkylene group may contain urones or optionally substituted triazone resins.
Beispiele für entsprechende N-Methylol-Harnstoff-Verbindungen sind gegebenenfalls modifizierte
N-Methylol-Hydroxyethylenharnstoff-Produkte, z.B. die Verbindungen der Formel
oder Methylolierungsprodukte
auf Basis von Propylenharnstoff oder Ethylenharnstoff/Melamin.
Bevorzugte Vernetzer sind gegebenenfalls modifizierte N-Methylol-Hydroxyethylenharnstoff-Verbindungen,
Methylolierungsprodukte auf Basis von Propylenharnstoff oder Ethylenharnstoff/Melamin
und insbesondere gegebenenfalls veretherte Melamin/Formaldehyd-Kondensationsprodukte.
Es können auch Mischungen von zwei oder mehreren verschiedenen wasserlöslichen
Vernetzern verwendet werden, z.B. eine aus einem unverätherten und einem
nur teilweise veretherten Melamin/Formaldehyd-Kondensationsprodukt bestehende Mischung.
Gewünschtenfalls kann die Druckpaste noch Vernetzungskatalysatoren, Säurespender wie
Butyrolacton oder Natriumhydrogenphosphat, Konservierungsmittel, Sequestriermittel, Emulgatoren,
wasserunlösliche Lösungsmittel, Oxidationsmittel oder Entlüftungsmittel enthalten.Examples of corresponding N-methylol-urea compounds are optionally modified N-methylol-hydroxyethylene urea products, for example the compounds of the formula or methylolation products based on propylene urea or ethylene urea / melamine.
Preferred crosslinkers are optionally modified N-methylol-hydroxyethylene urea compounds, methylolation products based on propylene urea or ethylene urea / melamine and in particular optionally etherified melamine / formaldehyde condensation products. Mixtures of two or more different water-soluble crosslinking agents can also be used, for example a mixture consisting of an unetherified and an only partially etherified melamine / formaldehyde condensation product.
If desired, the printing paste can also contain crosslinking catalysts, acid donors such as butyrolactone or sodium hydrogenphosphate, preservatives, sequestering agents, emulsifiers, water-insoluble solvents, oxidizing agents or deaerating agents.
Als Vernetzungskatalysatoren kommen für das erfindungsgemässe Verfahren z.B. alle üblicherweise
als Katalysator für die Knitter- und Krumpffreiausrüstung verwendeten Mittel in
Frage, wie sie aus dem Textilhilfsmittelkatalog 1991, Konradin Verlag R. Kohlhammer, Leinfelden-Echterdingen
1991, bekannt sind. Beispiele für geeignete Vernetzungskatalysatoren
sind anorganische Säuren, z.B. Phosphorsäure; Lewis-Säuren, z.B. Zinkchlorid, Zirkonoxychlorid,
NaBF4, AlCl3, MgCl2; Ammoniumsalze, z.B. Ammoniumsulfat, Ammoniumchlorid;
oder Hydrohalogenide, insbesondere Hydrochloride organischer Amine, z.B.
Als Konservierungsmittel kommen in Betracht vor allem formaldehydabgebende Mittel, wie z.B. Paraformaldehyd und Trioxan, vor allem wässrige, etwa 30 bis 40-gewichtsprozentige Formaldehydlösungen, als Sequestriermittel z.B. nitrilotriessigsaures Natrium, ethylendiamintetraessigsaures Natrium, vor allem Natrium-Polymetaphosphat, insbesondere Natrium-Hexametaphosphat, als Emulgatoren vor allem Addukte aus einem Alkylenoxid und einem Fettalkohol, insbesondere einem Addukt aus Oleylalkohol und Ethylenoxid, als wasserunlösliche Lösungsmittel hochsiedende, gesättigte Kohlenwasserstoffe, vor allem Paraffine mit einem Siedebereich von etwa 160 bis 210° C (sogenannte Lackbenzine), als Oxidationsmittel z.B. eine aromatische Nitroverbindung, vor allem eine aromatische Mono- oder Dinitrocarbonsäure oder -sulfonsäure, die gegebenenfalls als Alkylenoxidaddukt vorliegt, insbesondere eine Nitrobenzolsulfonsäure und als Entlüftungsmittel z.B. hochsiedende Lösungsmittel, vor allem Terpentinöle, höhere Alkohle, vorzugsweise C8- bis C10-Alkohole, Terpenalkohole oder Entlüftungsmittel auf Basis von Mineral- und/oder Silikonölen, insbesondere Handelsformulierungen aus etwa 15 bis 25 Gewichtsprozent eines Mineral- und Silikonölgemisches und etwa 75 bis 85 Gewichtsprozent eines C8-Alkohols wie z.B. 2-Ethyl-n-hexanol.Suitable preservatives are, above all, formaldehyde-releasing agents, such as, for example, paraformaldehyde and trioxane, especially aqueous, approximately 30 to 40 percent by weight formaldehyde solutions, and sequestering agents, for example sodium nitrilotriacetic acid, sodium ethylenediaminetetraacetic acid, especially sodium polymetaphosphate, in particular sodium hexametaphosphate, as emulsifiers especially adducts of an alkylene oxide and a fatty alcohol, especially an adduct of oleyl alcohol and ethylene oxide, as water-insoluble solvents, high-boiling, saturated hydrocarbons, especially paraffins with a boiling range of about 160 to 210 ° C (so-called mineral spirits), as an oxidizing agent, for example an aromatic nitro compound , especially an aromatic mono- or dinitrocarboxylic acid or sulfonic acid, which is optionally present as an alkylene oxide adduct, in particular a nitrobenzenesulfonic acid and as a deaerating agent, for example high-boiling solvents, especially turpentine oils re alcohol, preferably C 8 to C 10 alcohols, terpene alcohols or deaerating agents based on mineral and / or silicone oils, in particular commercial formulations of about 15 to 25 percent by weight of a mineral and silicone oil mixture and about 75 to 85 percent by weight of a C 8 alcohol such as 2-ethyl-n-hexanol.
Beim Bedrucken des Fasermateriales wird die Druckpaste ganzflächig oder stellenweise direkt auf das Fasermaterial aufgebracht, wobei Druckmaschinen üblicher Bauart, z.B. Tiefdruck-, Rotationssiebdruck-, Rouleauxdruck und Flachfilmdruckmaschinen zweckmässig eingesetzt werden. Das Bedrucken kan auch mittels Ink-jet Drucktechnik erfolgen.When printing on the fiber material, the printing paste becomes full or in places applied directly to the fiber material, printing machines of conventional design, e.g. Gravure, Rotary screen printing, Rouleaux printing and flat film printing machines useful be used. Printing can also be done using ink-jet printing technology.
Das Fasermaterial wird nach dem Bedrucken vorteilhafterweise getrocknet, vorzugsweise bei Temperaturen bis 150° C, insbesondere 80 bis 120° C, und anschliessend einem Hitzebehandlungsprocess unterworfen, um den Druck zu vervollständigen, bzw. den Farbstoff zu fixieren. After printing, the fiber material is advantageously dried, preferably at temperatures up to 150 ° C, in particular 80 to 120 ° C, and then a heat treatment process subjected to complete the print, or the dye to fix.
Die Hitzebehandlung kann durch ein Warmverweilverfahren, einen Thermosolierprocess oder vorzugsweise durch ein Dämpfverfahren (HT-Fixierung) durchgeführt werden.The heat treatment can be carried out by a warm dwell process, a thermal insulation process or preferably be carried out by a damping process (HT fixation).
Beim Dämpfverfahren wird das bedruckte Fasermaterial einer Behandlung in einem Dämpfer
mit gegebenenfalls überhitztem Dampf, zweckmässigerweise bei einer Temperatur von
95 bis 210° C, vorteilhafterweise 100 bis 180°C unterzogen.
Vorzugsweise wird das bedruckte Fasermaterial bei der HT-Fixierung während 2 bis 5 Minuten
bei 150 bis 170° C behandelt.In the steaming process, the printed fiber material is subjected to a treatment in a steamer with possibly superheated steam, advantageously at a temperature of 95 to 210 ° C., advantageously 100 to 180 ° C.
The printed fiber material is preferably treated for 2 to 5 minutes at 150 to 170 ° C. during HT fixation.
Die Fertigstellung der Drucke durch den sogenannten Thermosolierprocess kann nach einer
oder ohne Zwischentrocknung, z.B. bei einer Temperatur von 100 bis 210° C erfolgen. Vorzugsweise
erfolgt die Thermosolierung bei einer Temperatur von 120 bis 210° C, insbesondere
140 bis 180° C. Je nach der Temperatur kann die Thermosolierung 20 Sekunden bis 5
Minuten, vorzugsweise 30 Sekunden bis 4 Minuten dauern.
Üblicherweise wird die Thermosolierung während 1 bis 2 Minuten bei 190 bis 210° C durchgeführt.
Im Anschluss an den Druckprocess wird das bedruckte Fasermaterial in üblicher Weise ausgewaschen,
um nichtfixierten Farbstoff zu entfernen. Man behandelt dazu das Fasermaterial
beispielsweise bei 40° C bis Kochtemperatur mit Wasser, welchem gegebenenfalls eine Seife
oder ein synthetisches Waschmittel zugesetzt werden kann.The prints can be finished by the so-called thermal insulation process after or without intermediate drying, for example at a temperature of 100 to 210 ° C. The thermal insulation is preferably carried out at a temperature of 120 to 210 ° C., in particular 140 to 180 ° C. Depending on the temperature, the thermal insulation can take 20 seconds to 5 minutes, preferably 30 seconds to 4 minutes.
The thermal insulation is usually carried out at 190 to 210 ° C. for 1 to 2 minutes.
After the printing process, the printed fiber material is washed out in the usual way to remove unfixed dye. For this purpose, the fiber material is treated with water, for example at from 40 ° C. to boiling temperature, to which a soap or a synthetic detergent can optionally be added.
Die Ausführung des erfindungsgemässen Druckverfahrens erfolgt z.B. in der Weise, dass man eine Druckpaste, welche mindestens einen Farbstoff der Formel (1) und mindestens einen Pigmentfarbstoffbinder sowie gegebenenfalls weitere Hilfsmittel enthält, auf das Fasermaterial aufbringt, das bedruckte Fasermaterial trocknet und anschliessend durch eine Hitzebehandlung fixiert.The printing method according to the invention is carried out e.g. in the way that a printing paste containing at least one dye of the formula (1) and at least contains a pigment dye binder and optionally other auxiliaries on the fiber material applies, the printed fiber material dries and then through a Heat treatment fixed.
Die erfindungsgemäss verwendete Färbeflotte oder Druckpaste kann auf verschiedenartigen
Fasermaterialien, wie Wolle, Seide, Cellulose, Polyvinyl, Polyacrylnitril, Polyamid, Aramid,
Polypropylen, Polyester oder Polyurethan appliziert werden.
Bevorzugt sind polyesterhaltige und cellulosehaltige Fasermaterialien.
Als polyesterhaltige Fasermaterialien kommen solche Materialien in Betracht, die ganz oder
teilweise aus Polyester bestehen. Beispiele sind Celluloseesterfasern, wie z.B. Cellulose-21/2-acetatfasern
und -triacetatfasern, und besonders lineare Polyesterfasern, die gegebenenfalls
auch sauer modifiziert sind, welche z.B. durch Kondensation von Terephthalsäure
mit Ethylenglykol oder von lsophthalsäure oder Terephthalsäure mit 1,4-Bis(hydroxymethyl)-cyclohexan
erhalten werden, sowie Fasern aus Mischpolymeren von Terephthal- und Isophthalsäure
mit Ethylenglykol. Geeignet sind weiter polyesterhaltige Mischfasermaterialien,
d.h. Mischungen aus Polyester und anderen Fasern.The dye liquor or printing paste used according to the invention can be applied to various types of fiber materials, such as wool, silk, cellulose, polyvinyl, polyacrylonitrile, polyamide, aramid, polypropylene, polyester or polyurethane.
Polyester-containing and cellulose-containing fiber materials are preferred.
Suitable polyester-containing fiber materials are materials which consist entirely or partially of polyester. Examples are Celluloseesterfasern such as cellulose-2 1 / acetate 2 and cellulose triacetate fibers, and especially linear polyester fibers, optionally also acid-modified which, for example, by condensing terephthalic acid with ethylene glycol or of isophthalic acid or terephthalic acid with 1,4-bis ( hydroxymethyl) -cyclohexane are obtained, as well as fibers from copolymers of terephthalic and isophthalic acid with ethylene glycol. Also suitable are polyester-containing mixed fiber materials, ie mixtures of polyester and other fibers.
Als cellulosehaltige Fasermaterialien kommen solche Materialien in Betracht, die ganz oder teilweise aus Cellulose bestehen. Beispiele sind natürliche Fasermaterialien wie Baumwolle, Leinen oder Hanf, regenerierte Fasermaterialien wie z.B. Viskose, Polynosic oder Kupferkunstseide. Geeignet sind weiter cellulosehaltige Mischfasermaterialien, d.h. Mischungen aus Cellulose und anderen Fasern, insbesondere Baumwolle/Polyesterfasermaterialien.Suitable cellulose-containing fiber materials are those materials which are entirely or partly consist of cellulose. Examples are natural fiber materials such as cotton, Linen or hemp, regenerated fiber materials such as Viscose, polynosic or copper artificial silk. Also suitable are cellulose-containing mixed fiber materials, i.e. Mixtures made of cellulose and other fibers, especially cotton / polyester fiber materials.
Hauptsächlich werden Gewebe, Gewirke oder Bahnen dieser Fasern verwendet.Mainly fabrics, knitted fabrics or webs of these fibers are used.
Die nach dem erfindungsgemässen Verfahren erhältlichen Färbungen oder Drucke weisen gute Allgemeinechtheiten auf; sie besitzen z.B. gute Nassechtheiten, wie Wasch-, Wasser-, Seewasser-, Überfärbe- und Schweissechtheit, eine gute Chlorechtheit, Reibechtheit, Bügelechtheit und Plissierechtheit und zeichnen sich durch eine hohe Farbstärke und einen brillanten Farbton aus. Insbesondere zeichnen sich die nach dem erfindungsgemässen Verfahren erhältlichen Färbungen oder Drucke durch sehr gute Licht-, Sublimations- und Trockenreinigungsechtheiten aus.The dyeings or prints obtainable by the process according to the invention have good general fastnesses; e.g. they have good wet fastness properties, such as washing, water, Fastness to seawater, dyeing and sweating, good chlorine fastness, rubbing fastness, ironing fastness and pleating fastness and are characterized by a high color strength and a brilliant Hue off. In particular, they are distinguished by the process according to the invention available dyeings or prints due to very good fastness to light, sublimation and dry cleaning out.
Die nachfolgenden Beispiele dienen der Erläuterung der Erfindung. Darin bedeuten Teile Gewichtsteile und Prozente Gewichtsprozente. Die Temperaturen sind in Celsiusgraden angegeben. Die Beziehung zwischen Gewichtsteilen und Volumenteilen ist dieselbe wie diejenige zwischen Gramm und Kubikzentimeter.The following examples serve to explain the invention. In it parts mean Parts by weight and percentages by weight. The temperatures are given in degrees Celsius. The relationship between parts by weight and parts by volume is the same as that between grams and cubic centimeters.
2,23 g 1-Aminoanthrachinon werden in 20 ml 100%-iger Essigsäure verrührt und bei Raumtemperatur mit 1,7 ml einer 40%-igen Nitrosylschwefelsäure tropfenweise versetzt. Nach kurzem Ausreagieren trägt man 1,94 g der Pyridonverbindung der Formel ein.2.23 g of 1-aminoanthraquinone are stirred in 20 ml of 100% acetic acid and 1.7 ml of a 40% nitrosylsulfuric acid are added dropwise at room temperature. After a brief reaction, 1.94 g of the pyridone compound of the formula are carried a.
Anschliessend wird durch Zutropfen von gesättigter Natriumacetatlösung die Kupplung vervollständigt und der ausgefallene Farbstoff der Formel wird durch Filtration isoliert, mit heissem Wasser gewaschen und getrocknet.The coupling is then completed by dropwise addition of saturated sodium acetate solution and the precipitated dye of the formula is isolated by filtration, washed with hot water and dried.
26 g Anilin-4-(bis-N,N-hydroxyethyl)-sulfonamid werden in 200 ml Wasser mit 25 ml konz. Salzsäure gelöst, auf 0° C gekühlt und mit einer wässrigen Lösung von 6,9 g Natriumnitrit diazotiert. Die erhaltene Diazoverbindung wird mit Natriumacetatlösung abgestumpft und mit einer Lösung von 18 g der Kupplungskomponente der Formel versetzt. Der pH-Wert wird auf 5 angehoben. Der entstandene Farbstoff der Formel wird filtriert, mit Wasser gewaschen und getrocknet.26 g of aniline-4- (bis-N, N-hydroxyethyl) sulfonamide are concentrated in 200 ml of water with 25 ml. Hydrochloric acid dissolved, cooled to 0 ° C and diazotized with an aqueous solution of 6.9 g of sodium nitrite. The diazo compound obtained is blunted with sodium acetate solution and with a solution of 18 g of the coupling component of the formula transferred. The pH is raised to 5. The resulting dye of the formula is filtered, washed with water and dried.
Verfährt man wie im Beispiel 1 beschrieben, verwendet aber anstatt der 1,94 g der Kupplungskomponente der Formel (32) die stöchiometrische Menge der Kupplungskomponente der Formel so erhält man ein Farbstoffpulver der Formel The procedure is as described in Example 1, but instead of the 1.94 g of the coupling component of the formula (32), the stoichiometric amount of the coupling component of the formula is used this gives a dye powder of the formula
2,23 g 1-Aminoanthrachinon werden in 20 ml 100%-iger Essigsäure verrührt und bei Raumtemperatur
mit 1,7 ml einer 40%-igen Nitrosylschwefelsäure tropfenweise versetzt. Nach
kurzem Ausreagieren trägt man
1.41 g der Verbindung der Formel
ein, und tropft zur Vervollständigung der Kupplungsreaktion eine gesättigte Natriumace-tatlösung
zu.
Der ausgefallenen Farbstoff wird abfiltriert, mit heissem Wasser gewaschen und getrocknet. 2.23 g of 1-aminoanthraquinone are stirred in 20 ml of 100% acetic acid and 1.7 ml of a 40% nitrosylsulfuric acid are added dropwise at room temperature. After a short reaction you wear
1.41 g of the compound of the formula and a saturated sodium acetate solution is added dropwise to complete the coupling reaction.
The precipitated dye is filtered off, washed with hot water and dried.
Man erhält ein grünstichiges gelbes Farbstoffpulver der Formel A greenish yellow dye powder of the formula is obtained
Verfährt man wie im Beispiel 1 beschrieben, verwendet aber anstatt 2,23 g 1-Aminoanthrachinon die stöchiometrische Menge einer der in der Tabelle 1 aufgeführten Verbindungen (A) und anstatt 1,94 g der Kupplungskomponente der Formel (32) die stöchiometrische Menge einer der in der Tabelle 1 aufgeführten Kupplungskomponenten (B), so erhält man die in der Tabelle 1 angegebenen Farbstoffe der Formeln (12) bis (23). The procedure is as described in Example 1, but instead of 2.23 g of 1-aminoanthraquinone, the stoichiometric amount of one of the compounds (A) listed in Table 1 and instead of 1.94 g of the coupling component of the formula (32), the stoichiometric amount of one of the Coupling components (B) listed in Table 1, the dyes of the formulas (12) to (23) given in Table 1 are obtained.
Ein Baumwollgewebe wird mit einer Druckpaste, enthaltend
Man erhält einen goldgelben Druck mit guten Licht-, Sublimations- und Trockenreinigungsechtheiten.A cotton fabric is containing with a printing paste
A golden yellow print is obtained with good fastness to light, sublimation and dry cleaning.
Verfährt man wie in Beispiel 6 angegeben, verwendet aber anstatt 30,6 g einer 21,5%-igen wässrigen, mikrodispergierten Formulierung des Farbstoffes der Formel (10) die gleiche Menge des Farbstoffes der Formel (11a), der Formel (12) oder der Formel (22a) erhält man ebenfalls Drucke mit guten Licht-, Sublimations- und Trockenreinigungsechtheiten.The procedure is as given in Example 6, but instead of 30.6 g, a 21.5% strength is used aqueous, microdispersed formulation of the dye of formula (10) the same The amount of the dye of the formula (11a), the formula (12) or the formula (22a) is obtained also prints with good fastness to light, sublimation and dry cleaning.
Verfährt man wie in Beispiel 6 angegeben, verwendet aber anstatt eines Baumwollgewebes ein Polyestergewebe, erhält man ebenfalls einen goldgelben Druck mit guten Licht-, Sublimations- und Trockenreinigungsechtheiten.The procedure is as described in Example 6, but is used instead of a cotton fabric a polyester fabric, you also get a golden yellow print with good light, sublimation and fastness to dry cleaning.
Verfährt man wie in Beispiel 6 angegeben, verwendet aber anstatt eines Baumwollgewebes ein Polyester/Baumwolle-67/33-Mischgewebe, erhält man ebenfalls einen goldgelben Druck mit guten Licht-, Sublimations- und Trockenreinigungsechtheiten.The procedure is as described in Example 6, but is used instead of a cotton fabric a polyester / cotton 67/33 blend, you also get a golden yellow print with good fastness to light, sublimation and dry cleaning.
Ein Baumwollgewebe wird mit einer wässrigen Flotte, enthaltend
Man erhält eine goldgelbe Färbung mit guten Licht-, Sublimations- und Trockenreinigungsechtheiten.A cotton fabric is containing an aqueous liquor
A golden yellow color is obtained with good fastness to light, sublimation and dry cleaning.
Ein Baumwoll/Polyester (50/50)-Mischgewebe wird mit einer wässrigen Flotte, enthaltend
43 g/l einer 21,5%-igen wässrigen, mikrodispergierten Formulierung des Farbstoffes der
Formel
Man erhält eine gelbe Färbung mit guten Licht-, Sublimations- und Trockenreinigungsechtheiten.A cotton / polyester (50/50) blend fabric is mixed with an aqueous liquor containing 43 g / l of a 21.5% aqueous, microdispersed formulation of the dye of the formula
A yellow color is obtained with good fastness to light, sublimation and dry cleaning.
Claims (15)
D einen Rest eines unlöslichen organischen Farbstoffes der Phthalocyanin-, Perinon-, Indigoid-, Thioindigoid-, Dioxazin-, Diketopyrrolopyrrol-, lsoindolinon-, Perylen-, Chinacridon-, Metallkomplex-, Monoazo-, Disazo-, Trisazo- oder Anthrachinonreihe bedeutet, X ein hydrophiler, polarer Rest, und n 1, 2 oder 3 ist, und mindestens einen Pigmentfarbstoffbinder sowie gegebenenfalls weitere Hilfsmittel, auf das Fasermaterial aufbringt und anschliessend fixiert.A process for dyeing or printing fiber material by the pigment dyeing or printing process, which is characterized in that a dye liquor or a printing paste containing at least one dye of the formula
D represents a residue of an insoluble organic dye of the phthalocyanine, perinone, indigoid, thioindigoid, dioxazine, diketopyrrolopyrrole, isoindolinone, perylene, quinacridone, metal complex, monoazo, disazo, trisazo or anthraquinone series, X is a hydrophilic, polar radical, and n is 1, 2 or 3, and at least one pigment dye binder and, if appropriate, other auxiliaries, are applied to the fiber material and then fixed.
R26 ein Rest der Formel oder ist,
worin R16 C1-C4-Alkyl oder ein Rest X, R17 Wasserstoff, Cyano oder Carbamoyl, R18 Wasserstoff, C1-C4-Alkyl oder ein Rest X, R25 C1-C6-Alkyl und X ein hydrophiler, polarer Rest, sind, und der Phenyl- bzw. Naphthylrest in der Formel (7a) gegebenenfalls durch Halogen, Cyano oder Nitro substituiert ist.Dyes of the formula wherein
R 26 is a radical of the formula or is
wherein R 16 is C 1 -C 4 alkyl or a radical X, R 17 is hydrogen, cyano or carbamoyl, R 18 is hydrogen, C 1 -C 4 alkyl or a radical X, R 25 is C 1 -C 6 alkyl and X are a hydrophilic, polar radical, and the phenyl or naphthyl radical in the formula (7a) is optionally substituted by halogen, cyano or nitro.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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CH163497 | 1997-07-04 | ||
CH1634/97 | 1997-07-04 | ||
CH163497 | 1997-07-04 |
Publications (2)
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EP0889159A2 true EP0889159A2 (en) | 1999-01-07 |
EP0889159A3 EP0889159A3 (en) | 2000-09-13 |
Family
ID=4215045
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Application Number | Title | Priority Date | Filing Date |
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EP98810586A Withdrawn EP0889159A3 (en) | 1997-07-04 | 1998-06-25 | Process for pigment dyeing and printing |
Country Status (7)
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US (1) | US6007586A (en) |
EP (1) | EP0889159A3 (en) |
JP (1) | JPH1171531A (en) |
KR (1) | KR19990013526A (en) |
BR (1) | BR9802332A (en) |
ID (1) | ID20138A (en) |
TW (1) | TW406149B (en) |
Cited By (1)
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DE102015218510A1 (en) | 2015-09-25 | 2017-03-30 | Cht R. Beitlich Gmbh | Textile fabrics with denim-like features |
Families Citing this family (8)
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US6451070B1 (en) * | 1998-03-06 | 2002-09-17 | Basf Corporation | Ultraviolet stability of aramid and aramid-blend fabrics by pigment dyeing or printing |
JP4100594B2 (en) * | 2000-01-11 | 2008-06-11 | 株式会社リコー | Pigment dispersion and ink-jet ink using the dispersion |
EP1357221A1 (en) * | 2002-04-25 | 2003-10-29 | Cognis Kimya Sanayi ve Ticaret A.S. | Method for printing or dyeing cellulosic textiles |
US20090013921A1 (en) * | 2007-07-12 | 2009-01-15 | Hua Yun | Decorative outdoor home flag kit |
CN102191685A (en) * | 2011-03-16 | 2011-09-21 | 内蒙古鄂尔多斯羊绒集团有限责任公司 | Processing method for pigment printing of plush product |
JP6724328B2 (en) * | 2015-10-05 | 2020-07-15 | 日東紡績株式会社 | Chlorine resistant treated dyed fabric and chlorine resistant treated mixed dye composition |
JPWO2019151451A1 (en) * | 2018-01-31 | 2020-11-19 | 富士フイルム株式会社 | Dyeing composition, dyeing, and azo dye |
CN114921977A (en) * | 2022-06-15 | 2022-08-19 | 江苏泰慕士针纺科技股份有限公司 | Dyeing process for short-process pad dyeing of knitted fabric |
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DE2012153B1 (en) * | 1970-03-14 | 1971-12-30 | Hoechst Ag | Process for the production of monoazo pigment mixtures and their use for coloring |
US4319025A (en) * | 1979-08-04 | 1982-03-09 | Bayer Aktiengesellschaft | Anthraquinone-azomethine compounds, processes for their preparation and processes for dyeing synthetic fibre materials and for pigmenting organic macromolecular substances |
DE3208694A1 (en) * | 1982-03-11 | 1983-09-22 | Basf Ag, 6700 Ludwigshafen | Process for dyeing cellulose-containing textile material by the fix-printing method and novel dyes |
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US4153618A (en) * | 1976-04-22 | 1979-05-08 | Ciba-Geigy Corporation | Fluorescent pigments |
US4379089A (en) * | 1980-10-08 | 1983-04-05 | Sterling Drug Inc. | Polyaminoalkylenesulfonamidated disazo colorants |
US4536570A (en) * | 1980-10-08 | 1985-08-20 | The Hilton-Davis Chemical Co. | N-Aminoalkylenesulfonamido substituted disazo colorants |
US4376729A (en) * | 1980-10-08 | 1983-03-15 | Sterling Drug Inc. | Novel monoazo and disazo colorants |
US4379088A (en) * | 1980-10-08 | 1983-04-05 | Sterling Drug Inc. | N-Aminoalkylenesulfonamido substituted monoazo colorants |
US4412950A (en) * | 1980-10-08 | 1983-11-01 | Sterling Drug Inc. | Monoazo and disazo colorants |
US4448722A (en) * | 1981-02-19 | 1984-05-15 | The Hilton-Davis Chemical Co. | Phthalocyanines |
NZ221708A (en) * | 1986-09-10 | 1990-07-26 | Basf Australia | Textile printing and dyeing using hexamethoxymethyl melamine in a c 4-8 glycol and a non-cationic colourant |
DE4137476A1 (en) * | 1991-11-14 | 1993-05-19 | Basf Ag | USE OF PIGMENT PREPARATIONS FOR THE PRODUCTION OF PASTE, PRINTING INKS AND VARNISHES |
-
1998
- 1998-06-17 US US09/100,001 patent/US6007586A/en not_active Expired - Fee Related
- 1998-06-25 EP EP98810586A patent/EP0889159A3/en not_active Withdrawn
- 1998-06-26 ID IDP980925A patent/ID20138A/en unknown
- 1998-06-30 JP JP10183652A patent/JPH1171531A/en active Pending
- 1998-07-01 BR BR9802332A patent/BR9802332A/en not_active IP Right Cessation
- 1998-07-02 TW TW087110690A patent/TW406149B/en not_active IP Right Cessation
- 1998-07-02 KR KR1019980026524A patent/KR19990013526A/en not_active Application Discontinuation
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
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DE2012153B1 (en) * | 1970-03-14 | 1971-12-30 | Hoechst Ag | Process for the production of monoazo pigment mixtures and their use for coloring |
US4319025A (en) * | 1979-08-04 | 1982-03-09 | Bayer Aktiengesellschaft | Anthraquinone-azomethine compounds, processes for their preparation and processes for dyeing synthetic fibre materials and for pigmenting organic macromolecular substances |
DE3208694A1 (en) * | 1982-03-11 | 1983-09-22 | Basf Ag, 6700 Ludwigshafen | Process for dyeing cellulose-containing textile material by the fix-printing method and novel dyes |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
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DE102015218510A1 (en) | 2015-09-25 | 2017-03-30 | Cht R. Beitlich Gmbh | Textile fabrics with denim-like features |
WO2017050646A1 (en) | 2015-09-25 | 2017-03-30 | Cht R. Beitlich Gmbh | Textile fabrics with denim-like features |
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BR9802332A (en) | 1999-07-20 |
KR19990013526A (en) | 1999-02-25 |
JPH1171531A (en) | 1999-03-16 |
US6007586A (en) | 1999-12-28 |
EP0889159A3 (en) | 2000-09-13 |
ID20138A (en) | 1998-10-08 |
TW406149B (en) | 2000-09-21 |
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